Objective: Plantar pressure abnormalities have a significant impact on mobility and quality of life. Real-time pressure monitoring is essential in clinical and rehabilitation settings for assessing patient progress and refining treatment protocols. Instrumental and particularly smart insoles offer a promising solution by collecting biomechanical data during daily activities. However, determining the optimal combination of sensor type, number, and placement remains a key challenge for ensuring accurate and reliable measurements. This study proposes a methodology for identifying the most appropriate sensor technology for wearable insoles, with a focus on data accuracy, system efficiency, and practical applicability. Additionally, it examines the correlation between sensor signals and material behavior during compression testing. Methods: Two insole prototypes underwent compression testing: one equipped with a Force Sensitive Resistor (FSR) sensor and one with a piezoelectric sensor, both positioned at the heel. Three trials per prototype assessed consistency and repeatability. Real-time data acquisition utilized a microcontroller system, and signals were processed using a sixth-order Butterworth low-pass filter with a 5 Hz cutoff frequency to reduce noise. Results: FSR sensors demonstrated stable static responses but saturated rapidly beyond 20 N, with performance degradation observed after repeated loading cycles. Piezoelectric sensors exhibited excellent dynamic sensitivity with sharp voltage peaks but proved unable to measure sustained static pressure. Conclusions: FSR sensors are well-suited for static postural assessment and continuous pressure monitoring, while piezoelectric sensors excel in dynamic gait analysis. This comparative framework establishes a foundation for developing future smart insole systems that deliver accurate, real-time rehabilitation monitoring.